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H8520

Sigma-Aldrich

(±)-8-Hydroxy-2-(dipropylamino)tetralin hydrobromide

≥98%

Synonym(s):

(±)-2-Dipropylamino-8-hydroxy-1,2,3,4-tetrahydronaphthalene, (±)-8-Hydroxy-2-(dipropylamino)tetralin, (±)-8-OH-DPAT

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About This Item

Empirical Formula (Hill Notation):
C16H25NO · HBr
CAS Number:
87394-87-4
Molecular Weight:
328.29
MDL number:
MFCD00055158
UNSPSC Code:
12352100
PubChem Substance ID:
57654276
NACRES:
NA.22

Quality Level

100

Assay

≥98%

SMILES string

Br[H].CCCN(CCC)C1CCc2cccc(O)c2C1

InChI

1S/C16H25NO.BrH/c1-3-10-17(11-4-2)14-9-8-13-6-5-7-16(18)15(13)12-14;/h5-7,14,18H,3-4,8-12H2,1-2H3;1H

InChI key

BATPBOZTBNNDLN-UHFFFAOYSA-N

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Application

(±)-8-Hydroxy-2-(dipropylamino)tetralin hydrobromide is a potent and selective 5-hydroxytryptamine (5HT1A)-receptor agonist which is generally used as the standard in pharmacological studies.

Biochem/physiol Actions

Selective 5-HT1 agonist with high affinity for subtype 5-HT1A receptor.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
118M4103V
127M4022V
016M4071V
016M4070V
13150512

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Arylpiperazine agonists of the serotonin 5-HT 1A receptor preferentially activate cAMP signaling versus recruitment of β-arrestin-2.
Stroth N, et al.
Bioorganic & Medicinal Chemistry, 23(15), 4824-4830 (2015)
8-Hydroxy-2-(di-n-propylamino)tetralin, a new centrally acting 5-hydroxytryptamine receptor agonist.
L E Arvidsson et al.
Journal of medicinal chemistry, 24(8), 921-923 (1981-08-01)
S J Peroutka
Journal of neurochemistry, 47(2), 529-540 (1986-08-01)
Drug interactions with 5-HT1 (5-hydroxytryptamine type 1) binding site subtypes were analyzed in rat frontal cortex. 8-Hydroxy-N,N-dipropyl-2-aminotetralin (8-OH-DPAT) displays high affinity (Ki 3.3 +/- 1 nM) for 29 +/- 3% of total [3H]5-HT binding in rat frontal cortex and low
Improved preparation, chromatographic separation and X-ray crystallographic determination of the absolute configuration of the enantiomers of 8-hydroxy-2-(dipropylamino) tetralin (8-OH DPAT).
Karlsson A, et al.
Acta Chemica Scandinavica, 42, 231-236 (1988)
8-Hydroxy-2-(di-n-propylamino)-tetralin discriminates between subtypes of the 5-HT1 recognition site.
D N Middlemiss et al.
European journal of pharmacology, 90(1), 151-153 (1983-05-20)
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